2,6-Lutidine → HCID 11187483, compound

HRID 1951048Notes

Reaction equation

HRID 1951048 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[OH:16][C:17]1[C:30]2[C:29](=[O:31])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=2[CH:20]=[C:19](O)[CH:18]=1.N1C(C)=CC=CC=1C>C(Cl)Cl>[OH:16][C:17]1[C:30]2[C:29](=[O:31])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=2[CH:20]=[C:19]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:18]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 54675891,3-Dihydroxy-10H-acridin-9-one

Product 1

HCID 11187483HCID 11187483, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (3.1 mL, 18.4 mmol) was slowly added to a solution of 1,3-dihydroxy-10H-acridin-9-one (4.0 g, 17.6 mmol), and 2,6-lutidine (65 mL) in CH2Cl2 (180 mL) at 0° C. See J. Reisch et al., Liebigs Ann. Chem., pp. 685-689 (1991). The reaction then was allowed to slowly warm to room temperature. After 16 h, the reaction was concentrated, redissolved in EtOAc (250 mL), and washed with 10% citric acid (5×50 mL) water (2×25 mL), and brine (2×25 mL). The organics then were dried (Na2SO4), filtered, and concentrated. The crude material then was purified via Biotage chromatography using 5% EtOAc/hexanes as eluent to yield 1.77 g (28%) of trifluoromethanesulfonic acid 1-hydroxy-9-oxo-9,10-dihydro-acridin-3-yl ester as an orange solid. Rf=0.50 (50% EtOAc/hexanes). 1H NMR (DMSO-d6, 400 MHz) δ: 12.45 (s, 1H), 8.25 (d, 1H), 7.87 (dd, 1H), 7.59 (d, 1H), 7.40 (dd, 1H), 6.99 (s, 1H), 6.67 (s, 1H).

Workup

  1. customThe reaction
  2. concentrationthe reaction was concentrated
  3. dissolutionredissolved in EtOAc (250 mL)
  4. washwashed with 10% citric acid (5×50 mL) water (2×25 mL), and brine (2×25 mL)
  5. dry with materialThe organics then were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material then was purified via Biotage chromatography

Sources & evidence

ORD record
ord-951d5234578b41c294a0496eb712cc57
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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